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Stewart

$118+ Cheap flights from Pittsburgh to New Windsor (PIT - SWF)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/25. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — SWF
Apr 11 — Apr 181
Sat 4/11
Sat 4/18
1 adult, Economy
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Cheap flight deals from Pittsburgh to Stewart

Cheapest flights from Pittsburgh to Stewart
Explore the most affordable flight options available from Pittsburgh to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 12, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1510:45 am
PIT
-
SWF
1 stop24h 10m
Multiple Airlines
Thu 4/3011:45 am
SWF
-
PIT
1 stop12h 14m
Multiple Airlines
Deal found 3/10$259
This Kiwi.com deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/206:25 am
PIT
-
SWF
1 stop27h 13m
Multiple Airlines
Mon 6/15:53 pm
SWF
-
PIT
1 stop4h 58m
Multiple Airlines
Deal found 3/10$265
This Kiwi.com deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/206:35 am
PIT
-
SWF
1 stop27h 03m
Multiple Airlines
Sun 5/246:51 pm
SWF
-
PIT
1 stop28h 00m
Multiple Airlines
Deal found 3/8$288
This Kiwi.com deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2812:36 pm
PIT
-
SWF
1 stop5h 25m
Multiple Airlines
Sun 5/316:51 pm
SWF
-
PIT
1 stop28h 00m
Multiple Airlines
Deal found 3/11$290
This Kiwi.com deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/226:35 am
PIT
-
SWF
1 stop28h 20m
Multiple Airlines
Sun 4/2611:45 am
SWF
-
PIT
1 stop29h 35m
Multiple Airlines
Deal found 3/8$293
This Kiwi.com deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2911:38 am
PIT
-
SWF
1 stop7h 18m
Multiple Airlines
Sun 5/3110:28 am
SWF
-
PIT
1 stop23h 09m
Multiple Airlines
Deal found 3/11$314
This Kiwi.com deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/77:30 am
PIT
-
SWF
1 stop11h 15m
Multiple Airlines
Sat 8/1512:05 pm
SWF
-
PIT
1 stop28h 01m
Multiple Airlines
Deal found 3/12$334
This Kiwi.com deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/15:49 pm
PIT
-
SWF
1 stop17h 36m
Multiple Airlines
Sun 9/66:05 pm
SWF
-
PIT
1 stop17h 32m
Multiple Airlines
Deal found 3/10$337
This Kiwi.com deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/411:52 am
PIT
-
SWF
1 stop5h 51m
Multiple Airlines
Sun 6/710:28 am
SWF
-
PIT
1 stop13h 31m
Multiple Airlines
Deal found 3/8$338
This Kiwi.com deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2311:52 am
PIT
-
SWF
1 stop5h 57m
Multiple Airlines
Thu 4/3011:45 am
SWF
-
PIT
1 stop12h 14m
Multiple Airlines
Deal found 3/9$348
This Kiwi.com deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/293:04 pm
PIT
-
SWF
2 stops19h 51m
Multiple Airlines
Sun 5/311:45 am
SWF
-
PIT
1 stop21h 52m
Multiple Airlines
Deal found 3/11$350

Find flight deals from Pittsburgh to Stewart

Discover tips and strategies to find the most affordable flight options for your journey from Pittsburgh (PIT) to Stewart (SWF). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated March 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$259
(Kiwi.com)

One-way from

$118
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$184
Provider with most accurate pricing for Pittsburgh-New Windsor Stewart flight deals.
Search Deals
Provider most trusted by Cheapflights users for Pittsburgh-New Windsor Stewart flights.
Search Deals
From Pittsburgh to New Windsor Stewart
Search Deals
One-way flight from Pittsburgh to New Windsor Stewart
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($19 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Pittsburgh to Stewart that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 12, 2026.
Use the filters below to find and compare flights from Pittsburgh to New Windsor that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Fri 5/29

11:38 am-6:56 pm

1 stop7h 18m

New Windsor Stewart

Sun 5/31

10:28 am-9:37 am

1 stop23h 09m

$314
Quickest round-trip

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Sat 6/27

8:00 am-5:55 pm

1 stop9h 55m

New Windsor Stewart

Mon 6/29

5:55 pm-11:11 pm

1 stop5h 16m

$378

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Thu 5/14

11:52 am-5:25 pm

1 stop5h 33m

New Windsor Stewart

Sun 5/17

11:45 am-5:20 pm

1 stop29h 35m

$386

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Thu 6/11

11:52 am-5:43 pm

1 stop5h 51m

New Windsor Stewart

Sun 6/14

10:28 am-11:59 pm

1 stop13h 31m

$397

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Thu 5/21

12:36 pm-6:01 pm

1 stop5h 25m

New Windsor Stewart

Sun 5/24

6:51 pm-10:51 pm

1 stop28h 00m

$456

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Wed 4/22

3:04 pm-10:55 am

2 stops19h 51m

New Windsor Stewart

Sun 4/26

11:45 am-5:20 pm

1 stop29h 35m

$499

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Fri 7/17

9:18 pm-11:25 am

2 stops14h 07m

New Windsor Stewart

Tue 7/21

6:19 pm-3:34 pm

1 stop21h 15m

$505

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Fri 7/10

11:33 am-6:51 pm

1 stop7h 18m

New Windsor Stewart

Sun 7/12

6:30 pm-11:37 am

1 stop17h 07m

$526

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Thu 4/30

11:52 am-5:25 pm

1 stop5h 33m

New Windsor Stewart

Thu 5/7

7:47 pm-7:41 pm

1 stop23h 54m

$536

PittsburghNew Windsor

PIT - SWF

PITSWF

Pittsburgh

Fri 6/26

11:33 am-6:38 pm

1 stop7h 05m

New Windsor Stewart

Sun 6/28

10:28 am-11:04 pm

2 stops12h 36m

$631

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/10

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

Compare providers for flights from Pittsburgh to Stewart

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Pittsburgh to Stewart in March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Pittsburgh-New Windsor flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Pittsburgh-New Windsor flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Pittsburgh-New Windsor flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Pittsburgh-New Windsor flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Pittsburgh-New Windsor flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Pittsburgh to Stewart

Have a flexible travel schedule? Discover the best time to fly to Stewart from Pittsburgh with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Pittsburgh to New Windsor

What is the cheapest month to book a flight from Pittsburgh to New Windsor?

Currently, April is the cheapest month in which you can book a flight from Pittsburgh to New Windsor (average of $43). Flying from Pittsburgh to New Windsor in February is currently the most expensive (average of $93). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Related info for your journey

Find useful and relevant information for your journey from Pittsburgh to Stewart. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Pittsburgh to New Windsor?

    Allegiant Air can get you from Pittsburgh to New Windsor in just under 9h 55m. Your travel time can differ by up to . The distance from Pittsburgh to New Windsor is about 327 mi.

  • Can I find deals for flights from Pittsburgh to Stewart that include hotel bookings?

    Yes. In addition to deals on Pittsburgh to Stewart flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Pittsburgh to Stewart?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Pittsburgh to Stewart.

  • Can I find deals for business class flights from Pittsburgh to Stewart?

    Yes. Cheapflights offers flight deals from Pittsburgh to Stewart by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Pittsburgh to New Windsor?

    Currently, April is the cheapest month in which you can book a flight from Pittsburgh to New Windsor (average of $43). Flying from Pittsburgh to New Windsor in February is currently the most expensive (average of $93). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near New Windsor?

Book flights to New Windsor if you plan to visit one of these locations
Kingston

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